76546-68-4

Usage

InChI:InChI=1/C15H17NO2/c1-4-18-15(17)14-10-11(2)16(12(14)3)13-8-6-5-7-9-13/h5-10H,4H2,1-3H3

Upstream product

• 141-97-9 ethyl acetoacetate 
• 78-95-5 chloroacetone 
• 62-53-3 aniline 
• 41892-81-3 ethyl 2-acetyl-4-oxopentanoate 
• 90674-91-2 ethyl 2-acetyl-4-bromopent-4-enoate 
• 36600-70-1 ethyl 2-acetylpent-4-ynoate 
• 2049-86-7 Diethyl 2,3-diacetylsuccinate 
• 6287-35-0 ethyl 3-anilinocrotonate 
• 67-64-1 acetone 
• 83-24-9 2,5-dimethyl-1-phenyl-1H-pyrrole 
• 247168-00-9 2-[1-Phenylamino-eth-(E)-ylidene]-pent-4-enoic acid ethyl ester 
• 610-89-9 2-acetyl-pent-4-enoic acid ethyl ester 
• 247168-03-2 ethyl 5-(iodomethyl)-2-methyl-1-phenyl-4,5-dihydro-1H-pyrrole-3-carboxylate 

Downstream Products

• 3807-56-5 2,5-dimethyl-1-phenyl-1H-pyrrole-3-carboxylic acid 

Relevant academic research and scientific papers

Beta-LACTAMASE INHIBITOR

The present invention addresses the problem of providing a compound having a beta-lactamase inhibitory activity. The problem is solved by a compound which is represented by general formula (1) that represents a compound in which a specific location of a 5

Screening of a Custom-Designed Acid Fragment Library Identifies 1-Phenylpyrroles and 1-Phenylpyrrolidines as Inhibitors of Notum Carboxylesterase Activity

The Wnt family of proteins are secreted signaling proteins that play key roles in regulating cellular functions. Recently, carboxylesterase Notum was shown to act as a negative regulator of Wnt signaling by mediating the removal of an essential palmitoleate. Here we disclose two new chemical scaffolds that inhibit Notum enzymatic activity. Our approach was to create a fragment library of 250 acids for screening against Notum in a biochemical assay followed by structure determination by X-ray crystallography. Twenty fragments were identified as hits for Notum inhibition, and 14 of these fragments were shown to bind in the palmitoleate pocket of Notum. Optimization of 1-phenylpyrrole 20, guided by structure-based drug design, identified 20z as the most potent compound from this series. Similarly, the optimization of 1-phenylpyrrolidine 8 gave acid 26. This work demonstrates that inhibition of Notum activity can be achieved by small, drug-like molecules possessing favorable in vitro ADME profiles.

Quinoline derivatives and their use

The invention discloses a quinoline derivative and a usage thereof, a compound with a structure as shown in a formula (I) and or a pharmaceutically acceptable salt of the compound. The compound or the pharmaceutically acceptable salt thereof disclosed by the invention can be applied to the field of preparation of drugs for preventing or treating tumors.

Discovery of novel Tetrahydrobenzo[b]thiophene and pyrrole based scaffolds as potent and selective CB2 receptor ligands: The structural elements controlling binding affinity, selectivity and functionality

CB2-based therapeutics show strong potential in the treatment of diverse diseases such as inflammation, multiple sclerosis, pain, immune-related disorders, osteoporosis and cancer, without eliciting the typical neurobehavioral side effects of CB1 ligands. For this reason, research activities are currently directed towards the development of CB2 selective ligands. Herein, the synthesis of novel heterocyclic-based CB2 selective compounds is reported. A set of 2,5-dialkyl-1-phenyl-1H-pyrrole-3-carboxamides, 5-subtituted-2-(acylamino)/(2-sulphonylamino)-thiophene-3-carboxylates and 2-(acylamino)/(2-sulphonylamino)-tetrahydrobenzo[b]thiophene-3-carboxylates were synthesized. Biological results revealed compounds with remarkably high CB2 binding affinity and CB2/CB1 subtype selectivity. Compound 19a and 19b from the pyrrole series exhibited the highest CB2 receptor affinity (Ki= 7.59 and 6.15 nM, respectively), as well as the highest CB2/CB1 subtype selectivity (～70 and ～200-fold, respectively). In addition, compound 6b from the tetrahydrobenzo[b]thiophene series presented the most potent and selective CB2 ligand in this series (Ki= 2.15 nM and CB2 subtype selectivity of almost 500-fold over CB1). Compound 6b showed a full agonism, while compounds 19a and 19b acted as inverse agonists when tested in an adenylate cyclase assay. The present findings thus pave the way to the design and optimization of heterocyclic-based scaffolds with lipophilic carboxamide and/or retroamide substituent that can be exploited as potential CB2 receptor activity modulators.

Cross-dehydrogenative coupling between enamino esters and ketones: Synthesis of tetrasubstituted pyrroles

Tetrasubstituted pyrroles have been synthesized via the cross-dehydrogenative coupling between enamino esters and acetone. Silver carbonate proved to be an effective oxidant, and no transition metal catalyst is necessary.

An efficient procedure for the synthesis of polysubstituted pyrroles in an ionic liquid

The ionic liquid 1-butyl-3-methyl-imidazolium hydrogen sulfate, [bmim]HSO4, was used as a catalyst and reaction medium for the pyrrole synthesis, and a wide range of aliphatic, aromatic, heteroaromatic and carboxylic 1,4-diketones easily underwent condensations with aniline and ethylenediamine to form polysubstituted pyrroles. Sequential decarboxylation/Paal-Knorr pyrrole condensation was observed, which provides a new and facile approach to monoester pyrroles from 1,4-diketo-2,3-dicarboxylic acid esters.

Indium-catalyzed synthesis of furans and pyrroles via cyclization of α-propargyl-β-keto esters

In(OTf)3 or In(NTf2)3 effectively catalyze the cyclo-isomerization reaction of -propargyl - keto esters and their imine analogues to afford trisubstituted furans and pyrroles, respectively. Both terminal and internal alkyn

Simple and efficient access to 3-ethoxycarbonylpyrroles, naphthofurans

An efficient method was developed for the synthesis of pyrrole and furan derivatives from enamines, phenols, and naphthols. The key steps involve iodocyclization and alumina-induced dehydroiodination reactions. Georg Thieme Verlag Stuttgart.

Synthesis of 1,2,3,5-tetrasubstituted pyrrole derivatives from 2-(2-bromoallyl)-1,3-dicarbonyl compounds

2-(2-Bromoallyl)-1,3-dicarbonyl compounds are converted into β-enamino, β-hydrazino esters and ketones, followed by base-promoted cyclization, leading to the formation of the corresponding 1,2,3,5-tetrasubstituted pyrroles. 1,2,4- and 1,2,3,4-Substituted pyrroles are also isolated as minor products. Starting from the 2-(2-bromoallyl)-cyclohexane-1,3-dione the corresponding tetrahydro indolone is prepared in good yield.

Synthesis of N-substituted pyrrole and tetrahydroindole derivatives from alkenyl β-dicarbonyl compounds

The iodocyclization of a series of alkenyl-substituted β-enamino esters and ketones, followed by base-promoted dehydroiodination, led to the formation of the corresponding pyrrole or tetrahydroindole derivatives. In the absence of base, the iodo-β-enamino esters 5 and 7 underwent spontaneous aromatization after dehydroiodination, furnishing the 4, 5, 6, 7-N- substituted-tetrahydroindoles 19 and 20. All the elimination reactions proceeded smoothly, in yields ranging from 71% to 99%. Starting from the β- allyl-dimedone 21, it was possible to prepare the oxotetrahydroindole 24, in moderate overall yield.